JP2002363552A - Organometallic light-emitting material - Google Patents
Organometallic light-emitting materialInfo
- Publication number
- JP2002363552A JP2002363552A JP2002111334A JP2002111334A JP2002363552A JP 2002363552 A JP2002363552 A JP 2002363552A JP 2002111334 A JP2002111334 A JP 2002111334A JP 2002111334 A JP2002111334 A JP 2002111334A JP 2002363552 A JP2002363552 A JP 2002363552A
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- aryl
- emitter
- luminescent material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims abstract description 37
- 125000002524 organometallic group Chemical group 0.000 title description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 229910052751 metal Inorganic materials 0.000 claims abstract description 10
- 239000002184 metal Substances 0.000 claims abstract description 10
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 8
- VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical group [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 150000002739 metals Chemical class 0.000 claims abstract description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims abstract description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 239000011593 sulfur Substances 0.000 claims abstract description 4
- 239000002019 doping agent Substances 0.000 claims description 20
- 239000003446 ligand Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 238000000859 sublimation Methods 0.000 claims description 6
- 230000008022 sublimation Effects 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 238000007738 vacuum evaporation Methods 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 150000001247 metal acetylides Chemical group 0.000 claims description 3
- 238000004528 spin coating Methods 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 2
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical group N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 1
- 229910052798 chalcogen Inorganic materials 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000010410 layer Substances 0.000 description 17
- 238000000295 emission spectrum Methods 0.000 description 10
- 125000004122 cyclic group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- -1 8-hydroxyquinolinyl Chemical group 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
- 239000006193 liquid solution Substances 0.000 description 3
- 238000001757 thermogravimetry curve Methods 0.000 description 3
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- XYZNIJOLUAUPAL-UHFFFAOYSA-N [Pt+2].[C-]#[C-] Chemical compound [Pt+2].[C-]#[C-] XYZNIJOLUAUPAL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000000475 acetylene derivatives Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- HCIIFBHDBOCSAF-UHFFFAOYSA-N octaethylporphyrin Chemical compound N1C(C=C2C(=C(CC)C(C=C3C(=C(CC)C(=C4)N3)CC)=N2)CC)=C(CC)C(CC)=C1C=C1C(CC)=C(CC)C4=N1 HCIIFBHDBOCSAF-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000001443 photoexcitation Effects 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
【0001】[0001]
【発明の属する技術分野】本願は、2001年3月8日
出願の米国特許出願第60/274,142号の優先権
を主張するものである。本発明は、真空蒸着によって薄
層として沈着出来る、高効率且つ高輝度有機発光装置
(OLED)において電圧燐光エミッターとして作用す
る事の出来る本来別々の有機金属分子である発光材料に
関する。[0001] This application claims priority to US patent application Ser. No. 60 / 274,142, filed Mar. 8, 2001. The present invention relates to luminescent materials, which are essentially separate organometallic molecules that can be deposited as thin layers by vacuum evaporation and that can act as voltage phosphorescent emitters in high efficiency and high brightness organic light emitting devices (OLEDs).
【0002】[0002]
【従来の技術】タンとその共同研究者達(Tang and cowo
rkers)は、1987年に、初めて高性能の有機発光装置
(OLED)について報告した(Tang, C.W., et al., A
ppl. Phys. Lett. 51, 913 (1987))。彼らの発見は、発
光層と適当な有機基体の正孔輸送層とを含む多層構造の
採用を基礎とするものであった。Alq3(q=脱プロ
トン8−ヒドロキシキノリニル)が発光材料として選択
され、それが、(1)真空蒸着を使用して1000Å以
下の薄いフィルムを均一に形成出来る事、(2)良好な
電荷担体である事及び(3)強力な蛍光を発する事から
高性能である事を証明した。それ以来、OLED及びこ
れらの装置で使用される材料についての研究が隆盛を極
めた。実際、光電子関係の世界の殆ど全ての大きな化学
会社は、OLEDにおける或程度の利益を証明してき
た。明らかに、OLED技術は、スタンフォードリソー
スの市場報告で指摘されている様に(by David E. Mentl
ey, "The Market Potential for Organic Light-Emitti
ng Diode Displays," Commercial Report, available a
t http://www.stanfordresources.com)、市場の中に直
接且つ急速に入り込みつつある。陰極線管(CRT)、
液晶ディスプレー(LCD)及びプラズマディスプレー
と言った従来の技術に挑戦するOLEDの魅力は、2. Description of the Related Art Tan and its co-workers (Tang and cowo)
rkers) reported for the first time a high performance organic light emitting device (OLED) in 1987 (Tang, CW, et al., A.
ppl. Phys. Lett. 51, 913 (1987)). Their discovery was based on the adoption of a multilayer structure comprising a light-emitting layer and a suitable organic substrate hole transport layer. Alq 3 (q = deprotonated 8-hydroxyquinolinyl) is selected as the luminescent material, which can (1) be able to form thin films of 1000 ° or less uniformly using vacuum evaporation, (2) good It proved to be high-performance because it is a charge carrier and (3) it emits strong fluorescence. Since then, research on OLEDs and the materials used in these devices has prospered. In fact, almost every major chemical company in the optoelectronics world has demonstrated some benefit in OLEDs. Obviously, OLED technology has been noted in the Stanford Resources Market Report (by David E. Mentl
ey, "The Market Potential for Organic Light-Emitti
ng Diode Displays, "Commercial Report, available a
t http://www.stanfordresources.com), which is penetrating the market directly and rapidly. Cathode ray tube (CRT),
The appeal of OLEDs that challenge the traditional technologies of liquid crystal displays (LCDs) and plasma displays is
【0003】1)低い操作電圧、 2)薄い一体構造、 3)光を変調するのではなく発光する、 4)良好な発光効率、 5)全発色の可能性及び 6)高コントラスト及び解像度、 と言った事を含めて、多くの特徴と利点にその根拠を置
く。OLEDは、電気刺激によって可視光を発光する事
の出来る有機半導体と共に組み込まれる装置である。O
LEDの基本的なヘテロ構造は図1で示される。層は、
蒸発、回転キャスティング又は化学的セルフアセンブリ
ーで形成されても良い。厚味は、少数の単層(セルフア
センブルされたフィルム)から約1000〜2000Å
の範囲である。その様な装置の構造は、光学発光、即
ち、捕捉電荷の放射再結合の原因となる一般的なメカニ
ズムに一般的に依存する有機光電子材料の層の使用を基
本とする。DCバイアスの下では、電子は陰極(通常は
Ca、Al、Mg−Ag)から射出され、正孔が陽極
(通常は透明なインジウム錫酸化物(ITO))から有
機材料中に射出され、そこで、それらは、適用された場
において、電子輸送層(ETL)と正孔輸送層(HT
L)を横切って、それらが、好ましくは発光層中の分子
と出会って、或条件の下で放射減衰を経て可視光を与え
る発光励起状態(フレンケル励起子)を形成するまで移
動する。電圧発光材料は、多層ヘテロ構造と言われる構
造においてETLとHTLとの間の別々の発光層中に存
在しても良い。幾つかの場合では、又、緩衝層及び/又
はその他の機能層も装置の性能改善の為に導入される。
或いは、電圧発光エミッターがETL又はHTLとして
機能するのと同じ材料であるこれらのOLEDは、単一
層ヘテロ構造とも言われる。[0003] 1) low operating voltage, 2) thin monolithic structure, 3) emits light rather than modulate, 4) good luminous efficiency, 5) full color potential and 6) high contrast and resolution, Based on many features and benefits, including what was said. OLEDs are devices that are incorporated with organic semiconductors that can emit visible light upon electrical stimulation. O
The basic heterostructure of an LED is shown in FIG. The layers are
It may be formed by evaporation, rotary casting or chemical self-assembly. The thickness ranges from a small number of monolayers (self-assembled film) to about 1000-2000Å
Range. The construction of such devices is based on the use of layers of organic optoelectronic material that generally rely on optical emission, ie, the general mechanism responsible for radiative recombination of trapped charges. Under a DC bias, electrons are emitted from the cathode (usually Ca, Al, Mg-Ag) and holes are emitted from the anode (usually transparent indium tin oxide (ITO)) into the organic material, where , They, when applied, have an electron transport layer (ETL) and a hole transport layer (HT).
Across L), they preferably migrate until they encounter a molecule in the emissive layer and form a luminescent excited state (Frenkel exciton) which, under certain conditions, undergoes a radiation decay to give visible light. The electroluminescent material may be present in a separate emissive layer between the ETL and the HTL in a structure referred to as a multilayer heterostructure. In some cases, buffer layers and / or other functional layers are also introduced to improve device performance.
Alternatively, these OLEDs, which are the same material for which the voltage-emitting emitter functions as an ETL or HTL, are also referred to as single-layer heterostructures.
【0004】電荷担体層(HTL又はETL)中の主成
分として存在する発光材料に加えて、その他の有効な発
光材料がそれらの層にドーパントとして比較的低濃度で
存在して色の調律及び効率改善を行っても良い。ドーパ
ントが存在する場合は、電荷担体層中の主成分材料はホ
ストと呼ばれても良い。理想としては、ホスト及びドー
パントとして存在する材料は、ホストからドーパントへ
のエネルギー移動が高水準であり、高効率で高輝度で、
選択されたスペクトル領域の近くに集中した相対的に狭
いバンドで発光する様に合わされる。高発光効率の蛍光
エミッターがOLEDにおけるドーパントとして広く適
用されてきているが、燐光エミッターは、この領域では
無視されてきた。然しながら、電圧蛍光装置の量子効率
は、電気的励起からの電子−正孔再結合に基づく三重励
起子(75%)に比べて一重励起子(25%)の低い理
論比の為に制限される。これに対して、燐光エミッター
が使用される場合は、正孔から燐光エミッターへの潜在
的に高いエネルギー/電子移動が、顕著に優れた電圧発
光効率をもたらすかも知れない(Baldo, M. A., et al.,
Nature 395, 151 (1998) and Ma, Y. G., et al., Syn
th. Met. 94, 245 (1998))。幾つかの燐光OLED系が
作られて、実際に、比較的高効率で高輝度であることが
証明されている。[0004] In addition to the luminescent materials present as a major component in the charge carrier layers (HTL or ETL), other available luminescent materials are present in those layers at relatively low concentrations as dopants to provide color tuning and efficiency. Improvements may be made. When a dopant is present, the main component material in the charge carrier layer may be referred to as a host. Ideally, the materials present as host and dopant have a high level of energy transfer from the host to the dopant, high efficiency and high brightness,
It is tuned to emit in a relatively narrow band concentrated near the selected spectral region. While high emission efficiency fluorescent emitters have been widely applied as dopants in OLEDs, phosphorescent emitters have been neglected in this area. However, the quantum efficiency of voltage fluorescent devices is limited due to the lower theoretical ratio of single excitons (25%) compared to triple excitons (75%) based on electron-hole recombination from electrical excitation. . In contrast, if a phosphorescent emitter is used, the potentially high energy / electron transfer from the hole to the phosphorescent emitter may result in significantly better voltage emission efficiency (Baldo, MA, et al. .,
Nature 395, 151 (1998) and Ma, YG, et al., Syn
th. Met. 94, 245 (1998)). Several phosphorescent OLED systems have been created and, in fact, have proven to be relatively efficient and bright.
【0005】三原色、即ち、全色ディスプレー装置にお
ける構成成分層として使用されても良い赤、緑及び青の
一つに相当する電圧燐光発光を与える材料を使用して組
み立てられる事がOLEDにとっては望ましい。又、そ
の様な材料は、発光層の厚味を正確に調節する事の出来
る、高性能のOLED製造の一般的な方法である事が立
証されている真空蒸着法を使用して、フィルムとして沈
着する事の出来るものである事が望ましい。現に、最高
の効率と輝度は、エミッターとしてIr(ppy)
3(ppy=脱プロトン2−フェニルピリジン)を使用
する緑色電圧燐光装置で得られている(外部量子効率と
して15.4±0.2%、内部効率として殆ど100
%、最大輝度として105Cd/m2)(Adachi, C., et
al., Appl. Phys. Lett. 77, 904 (2000)。又、電圧燐
光ドーパントPt(OEP)(H2OEP=オクタエチ
ルポルフィリン)をベースとした飽和赤色光を発光する
OLEDは公開され特許にもなっている(Burrows, P.,
et al., U.S. Pat. No. 6,048,630)が、その最大輝度
は約500Cd/m2に過ぎない。オレンジ色OLED
においてドーパントとして環状金属化白金(II)コンプ
レックスPt(thpy)2(thpy=脱プロトン2
−(2−チオエニル)ピリジン)を、そしてホストとし
てPVK(ポリ(N−ビニル)カルバゾール)を使用す
る関連特許がある(Lamansky, S., et al., WO 00/5767
6)。然しながら、本発明者が使用してみたPt(I
I)コンプレックスは、昇華又は真空蒸着には適さず、
従って、高い運転電圧となる回転キャスティング法が適
用され、0.11%の量子効率と100Cd/m2の輝
度が22Vで得られた。It is desirable for OLEDs to be assembled using a material that provides voltage phosphorescence corresponding to one of the three primary colors, red, green and blue, which may be used as a component layer in a full color display device. . Such materials can also be used as films using vacuum deposition techniques that have been proven to be a common method of manufacturing high performance OLEDs that can accurately control the thickness of the light emitting layer. It is desirable to be able to deposit. In fact, the highest efficiency and brightness are Ir (ppy)
3 Obtained with a green voltage phosphorescent device using (ppy = deproton 2-phenylpyridine) (15.4 ± 0.2% as external quantum efficiency, almost 100 as internal efficiency)
%, Maximum brightness 10 5 Cd / m 2 ) (Adachi, C., et.
al., Appl. Phys. Lett. 77, 904 (2000). An OLED that emits saturated red light based on a voltage phosphorescent dopant Pt (OEP) (H 2 OEP = octaethylporphyrin) has been published and patented (Burrows, P.,
et al., US Pat. No. 6,048,630), but its maximum brightness is only about 500 Cd / m 2 . Orange OLED
In the above, a cyclic metalated platinum (II) complex Pt (thpy) 2 (thpy = deproton 2)
-(2-thioenyl) pyridine) and PVK (poly (N-vinyl) carbazole) as host are related patents (Lamansky, S., et al., WO 00/5767).
6). However, the Pt (I
I) The complex is not suitable for sublimation or vacuum evaporation,
Therefore, a rotating casting method that provides a high operating voltage was applied, and a quantum efficiency of 0.11% and a luminance of 100 Cd / m 2 were obtained at 22 V.
【0006】[0006]
【発明が解決しようとする課題】本発明は、高性能OL
EDにおいて電圧燐光エミッター又はドーパントとして
使用される新規な有機金属発光材料に関する。特に、本
発明は、発光性化合物、電子輸送化合物及び正孔輸送化
合物を含む適当なホスト材料に対して有効な量で添加さ
れる時に、近赤色範囲での発光色を調律し且つ装置効率
及び輝度を高める燐光エミッターのファミリーの設計、
合成、性質及び用途に関する。更に、本発明のこれらの
燐光エミッターの熱安定性は昇華を行うのに十分であ
り、真空蒸着法を使用して装置に容易に導入ができ、従
って、真空蒸着された材料で完全に調製された高性能電
圧燐光装置が実現される。SUMMARY OF THE INVENTION The present invention provides a high performance OL
Novel organometallic luminescent materials used as voltage phosphorescent emitters or dopants in EDs. In particular, the present invention, when added in an effective amount to a suitable host material, including a luminescent compound, an electron transport compound and a hole transport compound, tunes the emission color in the near red range and improves device efficiency and Design of a family of phosphorescent emitters to increase brightness,
It relates to synthesis, properties and uses. In addition, the thermal stability of these phosphorescent emitters of the present invention is sufficient to effect sublimation and can be easily introduced into equipment using vacuum deposition methods, and is therefore completely prepared from vacuum deposited materials. A high performance voltage phosphorescent device is realized.
【0007】[0007]
【課題を解決するための手段】本発明で使用する電圧燐
光エミッターのファミリーは、式I又はIIの化学構造
を持つ、白金を含むグループ10の金属のアセチリド
(アルキニル)コンプレックスである。The family of voltage phosphorescent emitters used in the present invention is an acetylide (alkynyl) complex of a platinum-containing group 10 metal having the chemical structure of formula I or II.
【0008】[0008]
【化2】 (ここで、E=グループ16の元素(硫黄を含む);M
=グループ10の金属(白金を含む);R1〜R14は、
それぞれ独立に、水素;ハロゲン;アルキル;置換アル
キル;アリール;ハロゲン、低級アルキル及び認知され
ている供与体並びに受容体基から成る群から選ばれた置
換体を持つ置換アリールから成る群から選ばれ、R
1は、(C≡C)nR15(ここで、(C≡C)は、炭素−
炭素三重結合アセチリド基を表し、nは1〜10であ
り、R15はアルキル、アリール、置換アリール及びトリ
(アルキル)シリルから選択される)から選択する事が
できる)。又、グループ16の元素はVIA族元素として
知られているものであり、又、グループ10の元素はVI
IIB族に属するものである。Embedded image (Where E = elements of group 16 (including sulfur); M
= Metals of group 10 (including platinum); R 1 to R 14 are
Each independently selected from the group consisting of hydrogen; halogen; alkyl; substituted alkyl; aryl; halogen, lower alkyl and substituted aryl having a substituent selected from the group consisting of recognized donor and acceptor groups; R
1 is (C≡C) n R 15 (where (C≡C) is carbon-
Represents a carbon triple bond acetylide group, n is 1 to 10, and R 15 can be selected from alkyl, aryl, substituted aryl and tri (alkyl) silyl). The elements of group 16 are known as VIA group elements, and the elements of group 10 are VI
It belongs to the IIB group.
【0009】熱質量分析によって証明される様に、これ
らのコンプレックスの幾つかは、〜400℃まで熱的に
安定である。これらのコンプレックスは良好な燐光エミ
ッターであり、光励起により液体溶液中で、及び電気刺
激によりOLEDにおいて強力なオレンジ色から赤色の
発光(λmax550〜630nm)を与える。Some of these complexes are thermally stable up to 400 ° C., as evidenced by thermal mass spectrometry. These complexes are good phosphorescent emitters, giving intense orange to red emission (λ max 550-630 nm) in liquid solutions by photoexcitation and in OLEDs by electrical stimulation.
【発明の実施の形態】一般に、本発明は、式I及びII
で定義された電圧燐光エミッターのファミリーの合成及
びOLED用途に関する。本願発明の特許請求の範囲
は、これら新規なコンプレックスの合成法及び発光材料
としてのそれらの使用を含む。これらのOLED用途
は、これらのコンプレックスが、真空蒸着、回転キャス
ティング又はその他の装置製造法によって構成成分とし
て導入されるOLEDを含む。本発明において、OLE
Dでエミッター又はドーパントとして使用する発光材料
は、一種以上の金属−アセチリド(金属−アルキニル)
基を含む。或いは、OLEDでエミッター又はドーパン
トとして使用する発光材料は、一種以上の白金−アセチ
リド(白金−アルキニル)基を含む。一つの実施態様で
は、OLEDでエミッター又はドーパントとして使用す
る発光材料は、一個の炭素原子と二個の窒素原子を使用
する三座配位子で配位された白金原子を含む事が出来
る。その他の実施態様では、OLEDでエミッター又は
ドーパントとして使用する発光材料は、脱プロトンフェ
ニルカルボニオン(carbonion)と2,2′−ビピリジン
を生じる三座配位子で配位された白金原子を含む。DETAILED DESCRIPTION OF THE INVENTION In general, the present invention provides compounds of the formulas I and II
And OLED applications. The claims of the present invention include methods for synthesizing these novel complexes and their use as luminescent materials. These OLED applications include OLEDs where these complexes are introduced as components by vacuum evaporation, spin casting or other device manufacturing methods. In the present invention, OLE
The luminescent material used as emitter or dopant in D is one or more metal-acetylides (metal-alkynyl)
Group. Alternatively, the luminescent materials used as emitters or dopants in OLEDs include one or more platinum-acetylide (platinum-alkynyl) groups. In one embodiment, the emissive material used as an emitter or dopant in the OLED can include a platinum atom coordinated with a tridentate ligand using one carbon atom and two nitrogen atoms. In another embodiment, the emissive material used as an emitter or dopant in the OLED comprises a deprotonated phenyl carbonion and a platinum atom coordinated with a tridentate ligand to yield 2,2'-bipyridine.
【0010】例示的実施態様では、OLEDでエミッタ
ー又はドーパントとして使用する発光材料は、式I又は
IIで表される化学構造を有することが出来る。In an exemplary embodiment, a luminescent material used as an emitter or dopant in an OLED can have a chemical structure represented by Formula I or II.
【化3】 (ここで、E=グループ16の元素(硫黄を含む);M
=グループ10の金属(白金を含む);R1〜R14は、
それぞれ独立に、水素;ハロゲン;アルキル;置換アル
キル;アリール;ハロゲン、低級アルキル及び認知され
ている供与体並びに受容体基から成る群から選ばれた置
換体を持つ置換アリールから成る群から選ばれ、R
1は、(C≡C)nR15(ここで、(C≡C)は、炭素−
炭素三重結合アセチリド基を表し、nは1〜10であ
り、R15はアルキル、アリール、置換アリール及びトリ
(アルキル)シリルから選択される)から選択する事が
できる)。一つの実施態様では、発光材料は、昇華又は
真空蒸着によって薄層として沈着することが出来る。そ
の他の実施態様では、発光材料は、回転被覆又はその他
の方法によってOLEDに組み立てることが出来る。Embedded image (Where E = elements of group 16 (including sulfur); M
= Metals of group 10 (including platinum); R 1 to R 14 are
Each independently selected from the group consisting of hydrogen; halogen; alkyl; substituted alkyl; aryl; halogen, lower alkyl and substituted aryl having a substituent selected from the group consisting of recognized donor and acceptor groups; R
1 is (C≡C) n R 15 (where (C≡C) is carbon-
Represents a carbon triple bond acetylide group, n is 1 to 10, and R 15 can be selected from alkyl, aryl, substituted aryl and tri (alkyl) silyl). In one embodiment, the luminescent material can be deposited as a thin layer by sublimation or vacuum evaporation. In other embodiments, the luminescent material can be assembled into the OLED by spin coating or other methods.
【0011】本発明は、一般に、有機金属発光材料のフ
ァミリーの合成と性質並びに高性能OLEDにおけるそ
の用途に関する。これら新規なコンプレックスは、次の
様な幾つかの化学的且つ構造的特徴を有する。 1)白金を含むグループ10の金属の環状金属化ジイミ
ンコンプレックスである、 2)中性分子である、 3)金属の周りの正方形平面配位環境、 4)(C^N^N)で定義される三座配位子が三つの配
位部位を占有する、そして、 5)アセチリド(アルキニル)基が第四の配位部位を占
有する。 ジイミンと環状金属化Pt(II)コンプレックス両方の
構造的且つ分光学的特徴を組み合せた[(C^N^N)
Pt(II)]コンプレックスのタイプは報告されている
((a) Lai, S. W., et al., Inorg. Chem. 38, 4046 (19
99). (b) Cheung, T. C., et al., J. Chem. Soc., Dal
ton Trans. 1645 (1996). (c) Lai, S.W., et al., Org
anometallics 18, 3327(1999). (d) Yip, J. H. K., et
al., Inorg. Chem. 39, 3537 (2000). (e) Neve, F.,
et al., Inorg. Chem. 36, 6150(1997))。これらの結果
は、これらのコンプレックスが、固体状態及び液体溶液
の両方において良好な室温燐光エミッターである事を証
明している。λmax530〜800nmの範囲で生起する
相対的に長命な発光は、三重項金属から配位子への電荷
移動(3MLCT)又は金属−金属から配位子への電荷
移動(3MMLCT)の励起状態に対して割り当てられ
た。The present invention generally relates to the synthesis and properties of a family of organometallic luminescent materials and their use in high performance OLEDs. These new complexes have several chemical and structural features, such as: 1) a cyclic metalated diimine complex of a group 10 metal containing platinum; 2) a neutral molecule; 3) a square planar coordination environment around the metal; 4) defined by (C ^ N ^ N). The tridentate ligand occupies three coordination sites, and 5) the acetylide (alkynyl) group occupies the fourth coordination site. Combining the structural and spectroscopic features of both diimines and cyclic metallated Pt (II) complexes [(C ^ N ^ N)
Pt (II)] complex type reported
((a) Lai, SW, et al., Inorg.Chem. 38, 4046 (19
99). (B) Cheung, TC, et al., J. Chem. Soc., Dal
ton Trans. 1645 (1996). (c) Lai, SW, et al., Org
anometallics 18, 3327 (1999). (d) Yip, JHK, et
al., Inorg. Chem. 39, 3537 (2000). (e) Neve, F.,
et al., Inorg. Chem. 36, 6150 (1997)). These results demonstrate that these complexes are good room temperature phosphorescent emitters in both solid state and liquid solutions. The relatively long-lived emission that occurs in the range of λ max 530-800 nm is due to charge transfer from triplet metal to ligand ( 3 MLCT) or metal-metal to ligand ( 3 MMLCT). Assigned to excited state.
【0012】本発明は、本発明の特に好ましい実施態様
について詳述されるが、これらの実施態様は例示的実施
例に過ぎず、本発明はそれらに限定されるものではない
事が理解される。コンプレックスの合成 式I又はIIで示される、アリール環上に異なる置換体
を持つ多数の三座環状金属化Pt(II)アリールアセチ
リドを合成した。While the present invention will be described in detail with reference to particularly preferred embodiments of the invention, it will be understood that these embodiments are merely illustrative and that the invention is not limited thereto. . Complex Synthesis A number of tridentate cyclic metallated Pt (II) aryl acetylides with different substituents on the aryl ring, as shown in Formula I or II, were synthesized.
【0013】[0013]
【化4】 合成方法はスキーム1で示される。Embedded image The synthesis method is shown in Scheme 1.
【0014】[0014]
【化5】 スキーム1 三座(C^N^N)配位子は、クレンケ法(Krohnke's m
ethod)(Krohnke, F. Synthesis 1 (1976))によって調製
された。様々なアセチレンがソノガシラ法(Sonogashir
a's method)(Takahashi, S. et al. Synthsis 627 (198
0))で調製された。Cl−結合前駆体[(C^N^N)
PtCl]は、コンステイブル条件下で調製された(Con
stable, e. wt al. J. Chem. Soc. Dalton Trans. 2251
(1992) and 443 (1990))。所望のコンプレックスは、
Cu(I)−有機アミン−触媒反応によって合成され
た。例えば、脱気したジクロロメタン(30mL)溶液
中の[(C^N^N)PtCl](0.33mmo
l)、末端のアセチレン(1mmol)及びEt3N
(3mL)の混合物にCuI(5mg)が添加された。
この懸濁液を12時間、窒素雰囲気下で、室温で、光の
存在無しで攪拌した。得られた混合物を回転蒸発して乾
燥させた。粗生成物をフラッシュクロマトグラフィー
(中性Al2O3、溶出液としてジクロロメタン)及び/
又はジクロロメタン/ジエチルエーテルからの再結晶に
よって精製した。例を表Iに列挙するがそれらに限定さ
れるものではない。Embedded image Scheme 1 The tridentate (C ^ N ^ N) ligand is synthesized by the Krohnke's method.
ethod) (Krohnke, F. Synthesis 1 (1976)). Various acetylenes are used in the Sonogashir Act
a's method) (Takahashi, S. et al. Synthsis 627 (198
0)). Cl-bond precursor [(C ^ N ^ N)
[PtCl] was prepared under stable conditions (Cont.
stable, e. wt al.J. Chem. Soc. Dalton Trans. 2251
(1992) and 443 (1990)). The desired complex is
It was synthesized by Cu (I) -organic amine-catalyzed reaction. For example, [(C ^ N ^ N) PtCl] (0.33 mmol) in a degassed dichloromethane (30 mL) solution
l), terminal acetylene (1 mmol) and Et 3 N
(3 mL) was added to CuI (5 mg).
The suspension was stirred for 12 hours under a nitrogen atmosphere at room temperature without the presence of light. The resulting mixture was rotary evaporated to dryness. The crude product was purified by flash chromatography (neutral Al 2 O 3 , dichloromethane as eluent) and / or
Or purified by recrystallization from dichloromethane / diethyl ether. Examples are listed in Table I, but are not limited thereto.
【0015】[0015]
【表1】 [Table 1]
【表2】 [Table 2]
【表3】 [Table 3]
【表4】 [Table 4]
【0016】[0016]
【表5】 [Table 5]
【0017】コンプレックスの熱安定性 理想的には、OLEDで使用される低分子量成分は昇華
する事ができ且つ通常の沈着条件において安定でなけれ
ばならない。本発明のコンプレックスの多くは〜400
℃まで熱的に安定であり、420℃以上の温度において
のみ金属白金となって分解する(図2及び3それぞれで
のコンプレックス2及び15に対するTGA曲線を参
照)。三座環状金属化配位子を含む本発明に開示のこれ
らのコンプレックスで観察された熱安定性は、昇華にお
いて不安定であるラムスキー等によって開示された二座
Pt(thpy)2エミッターとは著しい対照をなす。 Complex Thermal Stability Ideally, the low molecular weight components used in OLEDs must be able to sublime and be stable under normal deposition conditions. Many of the complexes of the present invention are ~ 400
It is thermally stable up to 400 ° C. and decomposes as platinum metal only at temperatures above 420 ° C. (see TGA curves for complexes 2 and 15 in FIGS. 2 and 3, respectively). The observed thermal stability of these complexes disclosed in the present invention containing a tridentate cyclic metallization ligand is significant compared to the bidentate Pt (thpy) 2 emitter disclosed by Ramski et al., Which is unstable in sublimation. Make a control.
【0018】コンプレックスの分光学的性質 本発明においては、Pt(II)上に集中する正電荷を
中和する、(C^N^N)Pt(II)部分へのアセチ
リド基の連結は、これらコンプレックスの安定性を高
め、更に、3MLCT発光を深色的に変化させる。式I
及びIIで示されるコンプレックスのファミリーは、液
体溶液中で強力なオレンジ色から赤色の光発光を表示す
る。本発明におけるこれらエミッターの特徴的な吸収及
び発光バンドの例を表IIに纏めた。表II 全てのデータは298Kで、脱気されたジクロロメタン
溶液で集められた点に注意。 Spectroscopic Properties of the Complex In the present invention, the linkage of the acetylide group to the (C ^ N ^ N) Pt (II) moiety, which neutralizes the positive charge concentrated on Pt (II) enhance stability of the complex, further, changing the 3 MLCT emission depth in color basis. Formula I
And II display strong orange to red light emission in liquid solution. Examples of characteristic absorption and emission bands of these emitters in the present invention are summarized in Table II. Table II Note that all data was collected at 298K in a degassed dichloromethane solution.
【0019】コンプレックス2及び15に対して例示さ
れた吸収及び発光スペクトルは図4と5のそれぞれに示
される。昇華に対するその安定性を持つ本発明のコンプ
レックスの強いオレンジ色から赤色への燐光は、これら
の材料が高性能OLEDにおいてエミッター又はドーパ
ントとして使用できる事を意味する。The absorption and emission spectra exemplified for complexes 2 and 15 are shown in FIGS. 4 and 5, respectively. The strong orange-to-red phosphorescence of the inventive complex with its stability to sublimation means that these materials can be used as emitters or dopants in high performance OLEDs.
【0020】有機発光装置 香港市立大学のリー教授(Prof. S. T. Lee)によって組
み立てられた様な本発明のコンプレックスを使用する装
置は、図6で示される様な多層ヘテロ構造を有する。上
述の白金コンプレックスを含む全ての有機層はITO基
体上に真空蒸着された。NPB(N,N′−ジ−1−ナ
フチル−N,N′−ジフェニル−ベンジジン)とAlq
3(q=8−ヒドロキシキノリニル)は、それぞれ、正
孔輸送と電子輸送層として使用された。BCP(2,9
−ジメチル−4,7−ジフェニル−1,10−フェナン
トロリン、バソクプロイン)は発光帯域内で励起子を拘
束する為に使用された。マグネシウム銀合金は陰極とし
て使用された。選択されたPtコンプレックスは、燐光
エミッターとして導電性ホスト材料CBP(4,4′−
N,N′−ジカルバゾール−ビフェニル)中にドープさ
れた。最適なドーピング水準は、2、4及び6%で調整
され、Ptコンプレックスからの電圧発光が観察され
た。本発明を更に例示する為に以下に多数の実施例を列
挙する。 Organic Light Emitting Devices Devices using the complex of the present invention, such as those assembled by Prof. ST Lee of the City University of Hong Kong, have a multilayer heterostructure as shown in FIG. All organic layers, including the platinum complex described above, were vacuum deposited on ITO substrates. NPB (N, N'-di-1-naphthyl-N, N'-diphenyl-benzidine) and Alq
3 (q = 8-hydroxyquinolinyl) was used as the hole transport and electron transport layers, respectively. BCP (2, 9
-Dimethyl-4,7-diphenyl-1,10-phenanthroline, bathocuproine) was used to constrain excitons in the emission band. Magnesium silver alloy was used as the cathode. The selected Pt complex has a conductive host material CBP (4,4'-) as a phosphorescent emitter.
N, N'-dicarbazole-biphenyl). Optimal doping levels were adjusted at 2, 4 and 6% and electroluminescence from the Pt complex was observed. A number of examples are listed below to further illustrate the invention.
【0021】[0021]
【実施例】〔実施例1〕コンプレックス2をエミッター
として使用した。ドーピング水準が2%の装置の代表的
な電圧発光スペクトル、電流−電圧(I−V)と輝度−
電圧(B−V)曲線、及び発光効率−電流密度曲線が図
7で示される。ターンオン電圧:〜5V;最大輝度:1
2Vで9600Cd/m2;最大効率:25mA/cm2
で4.2Cd/A。電圧発光スペクトルにおいて、56
0〜630nmのバンド近くに、ホストとドーパントと
の間の不十分なエネルギー移動を示す430nmのピー
クが観察された。EXAMPLES Example 1 Complex 2 was used as an emitter. Typical voltage emission spectrum, current-voltage (IV) and luminance-for a device with a doping level of 2%
The voltage (BV) curve and the luminous efficiency-current density curve are shown in FIG. Turn-on voltage: ~ 5V; Maximum brightness: 1
9600 Cd / m 2 at 2 V; maximum efficiency: 25 mA / cm 2
4.2 Cd / A. In the voltage emission spectrum, 56
Near the 0-630 nm band, a 430 nm peak was observed indicating poor energy transfer between host and dopant.
【0022】〔実施例2〕4%のドーピング水準で、エ
ミッターとしてコンプレックス2を使用する装置の性能
が図8に示される。ターンオン電圧:〜5V;最大輝
度:10Vで7900Cd/m2;最大効率:30mA
/cm2で2.4Cd/A。このドーピング水準では、
ホストとドーパントとの間のエネルギー移動は飽和され
てホストからの発光が回避された。EXAMPLE 2 The performance of an apparatus using Complex 2 as an emitter at a doping level of 4% is shown in FIG. Turn-on voltage: 55 V; Maximum luminance: 7900 Cd / m 2 at 10 V; Maximum efficiency: 30 mA
2.4 Cd / A at / cm 2 . At this doping level,
The energy transfer between the host and the dopant was saturated to avoid light emission from the host.
【0023】〔実施例3〕エミッターとしてコンプレッ
クス3が使用された。4%のドーピング水準の装置の性
能は図9に示される。室温のジクロロメタン溶液中のこ
れらのコンプレックスによって示される燐光発光の傾向
と一致している深色性の電圧発光が観察された(λmax
580nm)。ターンオン電圧:〜5V;最大輝度:1
2Vで4000Cd/m2;最大効率:20mA/cm2
で1.4Cd/A。Example 3 Complex 3 was used as an emitter. The performance of the device with a doping level of 4% is shown in FIG. A deep-colored voltage emission was observed (λ max), which is consistent with the tendency for phosphorescence exhibited by these complexes in a dichloromethane solution at room temperature.
580 nm). Turn-on voltage: ~ 5V; Maximum brightness: 1
4000 Cd / m 2 at 2 V; maximum efficiency: 20 mA / cm 2
At 1.4 Cd / A.
【0024】〔実施例4〕エミッターとしてコンプレッ
クス16が使用された。4%のドーピング水準の装置の
性能は図10に示される。電圧発光は、振電的に構造化
された発光スペクトル(λmax610nm、660n
m)を持つ赤色であった。ターンオン電圧:〜5V;最
大輝度:13Vで3200Cd/m2;最大効率:30
mA/cm2で1.0Cd/A。一般的に、本発明の式
I及びIIで示される様な有機金属発光材料は、高効率
且つ高輝度のオレンジ色から赤色光のOLEDに適用で
きる新規な電圧燐光エミッターである事が証明された。
ここに開示の本発明の実施態様は、上述の目的を果たす
のに十分適しているものであることは明らかであり、多
数の変更とその他の実施態様は当業者によって実施され
るであろうし、又、添付の特許請求の範囲は、本発明の
真の精神と範囲内に存在するその様な変更と実施態様の
全てを包含するものである。Example 4 A complex 16 was used as an emitter. The performance of the device with a doping level of 4% is shown in FIG. The electroluminescence is a vibratory structured emission spectrum (λ max 610 nm, 660 n
m) was red. Turn-on voltage: 55 V; Maximum brightness: 3200 Cd / m 2 at 13 V; Maximum efficiency: 30
1.0 Cd / A at mA / cm 2 . In general, organometallic luminescent materials such as those of formulas I and II of the present invention have proven to be novel voltage phosphorescent emitters applicable to highly efficient and bright orange to red OLEDs. .
Obviously, the embodiments of the invention disclosed herein are well suited to accomplish the above objects, and numerous modifications and other embodiments will be practiced by those skilled in the art, It is intended that the appended claims cover all such modifications and embodiments that come within the true spirit and scope of the invention.
【図1】OLEDの一般的なヘテロ構造を示す。FIG. 1 shows a general heterostructure of an OLED.
【図2】コンプレックス2のTGA曲線を示す。FIG. 2 shows a TGA curve of Complex 2.
【図3】コンプレックス15のTGA曲線を示す。FIG. 3 shows a TGA curve of Complex 15.
【図4】298Kにおけるジクロロメタン中のコンプレ
ックス2の紫外線吸収力と発光スペクトルを示す。FIG. 4 shows the UV absorbance and emission spectrum of Complex 2 in dichloromethane at 298K.
【図5】298Kにおけるジクロロメタン中のコンプレ
ックス15の紫外線吸収力と発光スペクトルを示す。FIG. 5 shows the UV absorbance and emission spectrum of Complex 15 in dichloromethane at 298K.
【図6】本発明におけるOLEDのヘテロ構造を示す。FIG. 6 shows a heterostructure of an OLED according to the present invention.
【図7】2%のドーピング水準を持つ、エミッターとし
てコンプレックス2を使用する装置の電圧発光スペクト
ル、電流−電圧(I−V)と輝度−電圧(B−V)及び
発光効率−電流密度曲線を示す。FIG. 7 shows the voltage emission spectrum, current-voltage (IV) and luminance-voltage (BV) and luminous efficiency-current density curves of a device using Complex 2 as an emitter with a doping level of 2%. Show.
【図8】4%のドーピング水準を持つ、エミッターとし
てコンプレックス2を使用する装置の電圧発光スペクト
ル、電流−電圧(I−V)と輝度−電圧(B−V)及び
発光効率−電流密度曲線を示す。FIG. 8 shows the voltage emission spectrum, current-voltage (IV) and luminance-voltage (BV) and luminous efficiency-current density curves of a device using Complex 2 as an emitter with a doping level of 4%. Show.
【図9】4%のドーピング水準を持つ、エミッターとし
てコンプレックス3を使用する装置の電圧発光スペクト
ル、電流−電圧(I−V)と輝度−電圧(B−V)及び
発光効率−電流密度曲線を示す。FIG. 9 shows the voltage emission spectrum, current-voltage (IV) and luminance-voltage (BV) and luminous efficiency-current density curves of a device using Complex 3 as an emitter with a doping level of 4%. Show.
【図10】4%のドーピング水準を持つ、エミッターと
してコンプレックス16を使用する装置の電圧発光スペ
クトル、電流−電圧(I−V)と輝度−電圧(B−V)
及び発光効率−電流密度曲線を示す。FIG. 10: Voltage emission spectrum, current-voltage (IV) and luminance-voltage (BV) of a device using complex 16 as an emitter with a doping level of 4%.
And a luminous efficiency-current density curve.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 マイケル チ−ワン チャン 中華人民共和国 香港 ポクフラム ロー ド 75 フェアヴュー コート 9ビー Fターム(参考) 3K007 AB02 AB03 AB04 AB18 DB03 4H050 AA01 AA03 AB91 WB11 WB14 WB21 ──────────────────────────────────────────────────の Continued on the front page (72) Inventor Michael Chi-Wan Chang Hong Kong Pokhum Road 75 Fairview Court 9B F-term (Reference) 3K007 AB02 AB03 AB04 AB18 DB03 4H050 AA01 AA03 AB91 WB11 WB14 WB21
Claims (7)
ド基を含む、有機発光装置でエミッター又はドーパント
として使用する為の発光材料。1. A luminescent material for use as an emitter or dopant in an organic light emitting device, comprising one or more metal-acetylide groups coordinated to a metal.
ド基を含む、有機発光ダイオードでエミッター又はドー
パントとして使用する為の発光材料。2. A luminescent material for use as an emitter or dopant in an organic light emitting diode, comprising one or more metal-acetylide groups coordinated to platinum.
る、白金に配位した三座配位子を含む、有機発光ダイオ
ードでエミッター又はドーパントとして使用する為の発
光材料。3. A luminescent material for use as an emitter or dopant in an organic light emitting diode, comprising a tridentate ligand coordinated to platinum using one carbon atom and two nitrogen atoms.
ビピリジンから選ばれたジイミン基、及びフェニル、ア
リール及びヘテロ原子含有アリールから選ばれた脱プロ
トン芳香族基を使用する、白金に配位した三座配位子を
含む、有機発光ダイオードでエミッター又はドーパント
として使用する為の発光材料。(4) 2,2'-bipyridine and substituted 2,2'-
An emitter or dopant in an organic light emitting diode, including a tridentate ligand coordinated to platinum, using a diimine group selected from bipyridine and a deprotonated aromatic group selected from phenyl, aryl and heteroatom containing aryl Luminescent material for use as.
る、有機発光ダイオードでエミッター又はドーパントと
して使用する為の発光材料。 【化1】 (ここで、E=グループ16の元素(硫黄を含む);M
=グループ10の金属(白金を含む);R1〜R14は、
それぞれ独立に、水素;ハロゲン;アルキル;置換アル
キル;アリール;ハロゲン、低級アルキル及び認知され
ている供与体並びに受容体基から成る群から選ばれた置
換体を持つ置換アリールから成る群から選ばれ、R
1は、(C≡C)nR15(ここで、(C≡C)は、炭素−
炭素三重結合アセチリド基を表し、nは1〜10であ
り、R15はアルキル、アリール、置換アリール及びトリ
(アルキル)シリルから選択される)から選択する事が
できる)。5. A luminescent material having the chemical structure of formula I or II for use as an emitter or dopant in an organic light emitting diode. Embedded image (Where E = elements of group 16 (including sulfur); M
= Metals of group 10 (including platinum); R 1 to R 14 are
Each independently selected from the group consisting of hydrogen; halogen; alkyl; substituted alkyl; aryl; halogen, lower alkyl and substituted aryl having a substituent selected from the group consisting of recognized donor and acceptor groups; R
1 is (C≡C) n R 15 (where (C≡C) is carbon-
Represents a carbon triple bond acetylide group, n is 1 to 10, and R 15 can be selected from alkyl, aryl, substituted aryl and tri (alkyl) silyl).
せる事のできる、請求項1〜5の何れか一項に記載の発
光材料。6. A luminescent material according to claim 1, which can be deposited as a thin layer by sublimation or vacuum evaporation.
発光ダイオードに組み立てる事の出来る、請求項1〜5
の何れか一項に記載の発光材料。7. An organic light-emitting diode which can be assembled using spin coating or other methods.
The luminescent material according to any one of the above.
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Also Published As
Publication number | Publication date |
---|---|
US20070148334A1 (en) | 2007-06-28 |
TWI243197B (en) | 2005-11-11 |
JP3965319B2 (en) | 2007-08-29 |
US20020179885A1 (en) | 2002-12-05 |
US20070104978A1 (en) | 2007-05-10 |
US7026480B2 (en) | 2006-04-11 |
US7595119B2 (en) | 2009-09-29 |
HK1049679B (en) | 2006-12-08 |
HK1049679A1 (en) | 2003-05-23 |
US7695758B2 (en) | 2010-04-13 |
CN1267525C (en) | 2006-08-02 |
CN1381545A (en) | 2002-11-27 |
US20060175605A1 (en) | 2006-08-10 |
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